Page Points

1 ______ (12)

2 ______ (12)

3 ______ (22)

4 ______ (24)

5 ______ (17)

6 ______ (13)

Total ______ (100)

1 (a) Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when applicable. (6 pts)

(b) (6 pts) Provide structures for the following molecules.

Propyl-2,3-dimethylpentanoate 2-methoxybutanoyl chloride N,N-diethylbenzamide

2. Rank the following compounds with regard to expected reactivity toward nucleophilic acyl substitution. Label the most reactive compound 1 and the least reactive compound 4. (4 pts)

2.5 Predict the product of the following reaction. (2 pts)

3. Show the mechanism for an acid catalyzed hydroylisis of a nitrile to an acid. (6 pts)

4. Circle the most acidic compound in each of the following pairs of compounds. (4 pts)

5. Draw the structure of the lactone formed from 4-hydroxybutanoic acid. (3 pts)

6. Draw the structures of the products of the following reactions. (15 pts)

7. Draw the structures of the products of the following reactions. (24 pts)

8. Fill in the reagents necassary to complete the following reactions. (12 pts)

9. What are the starting materials for the following polymer. (2 pts)

10. Fill in the reagents above the arrows to complete the following synthetic route. (3 pts)

11. Show all the steps and reagents needed to complete the following transformation. A retrosynthetic approach (start at the product and work backwards) may be helpful. (6 pts)

12 . Draw three resonance structures for the intermediate formed after adding a proton (H+) to the ester shown below. Use arrows to move electrons. (3 pts)

13. Show a complete mechanism for the following reaction. (4 pts)